Carolyn Bessette Kennedy

Posted by Meghan
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JFK Jr. and Carolyn, in Jean Paul Gaultier, at the White House Correspondants Dinner, Washington DC, May 1, 1999.

Carolyn Bessette’s meteoric rise from working as a Calvin Klein shop girl in Boston to marrying into America’s most famous family by way of America’s most desired bachelor is the stuff of modern fairy tales. The climb, however, was less intentional than fated––Carolyn was voted “the ultimate beautiful person” in her high school yearbook, had a promising career in fashion PR, and dated several high profile men before finally settling on John F. Kennedy Jr., including Alessandro Benetton (as in United Colors of Benetton, to which he was the heir) and NHL hockey player John Cullen. Following a modest upbringing in Greenwich, Connecticut, Carolyn attended Boston University and from there landed a job working at a Calvin Klein store in Boston, which eventually led her to a position working PR for the company in the early 90s. She enjoyed a kind of success and notoriety in the fashion industry and as a darling of the downtown n!ightlife scene before her infamous courtship with JFK Jr.

From the earliest inklings of a relationship between Carolyn Bessette and JFK Jr., comparison’s between Carolyn and John’s mother, Jacqueline Kennedy Onassis, abounded. CBK and Jackie O each possessed an ease and coolness to their styles that were easily adored by many but never easily imitated, both of which came to define a generation. Carolyn Bessette Kennedy became America’s princess of minimal––clean lines, neutral tones, and always appropriate for the occasion. There was something to her style which made her look seem slightly avant garde, namely her approach to pairing silhouettes which were often boxy and seemingly unflattering b!ut which looked impeccable on her.

Carolyn was known for her penchant for Yohji Yamamoto, Prada, Miu Miu, Calvin Klein, and a then-unknown Narciso Rodriguez. She was rarely seen without her black Birkin bag or her Selima “Aldo” sunglasses––their very narrow oval shape is decidedly 90s in the best way. Never one to show too much skin, her modest sense of dress was more cooly clever than prudish and was done in such a way that hinted at her wit and vivacity (many wrongfully mistook her polished look and aloof public presence as indicators of a frigid personality). Beauty wise, her platinum blonde hair inspired legions of women from New York and beyond to head to the hair salon. She was also famous for wearing Face Stockholm’s “Cranberry Veil” lipstick, an elegant sheer berry red, and her signature scent was Egyptian musk. In the few years that Carolyn Bessette Kennedy was in the public light, she managed to establish herself as one of the best dressed women in America––that her look feels equally as relevant and modern today is a testament to the immaculate taste of a style icon gone too soon.

(L) Carolyn during her earlier modeling days. (R) Kate Moss and Carolyn Bessette Kennedy at a Calvin Klein event, 1992.


(L) The wedding of Carolyn Bessette and John F. Kennedy Jr., Cumberland Island, Georgia, September 1996. (R) JFK Jr. and Carolyn, New York City, 1996.


(L) Carolyn at The Blue Room, New York, January 1999. (M) JFK Jr. and Carolyn in a Yohji Yamamoto Jacket at the Municipal Arts Society gala, 1997. (R) Carolyn Bessette Kennedy in Yohji Yamamoto blouse and skirt.


(L) Carolyn in Yohji Yamamoto coat at the opening of the Krizia Exhibit at the Grey Art Gallery, New York City, April 14, 1999. (R) Carolyn by Bruce Weber in 1997, published in Vanity Fair, September 1999.


(L) Carolyn at the Kennedy Compound, Hyannis Port, Massachusetts, Labor Day Weekend, 1995. (M) Carolyn in a vintage leopard coat, New York City, December 1997. (R) Carolyn walking her dog, New York City.


(L) JFK Jr. and Carolyn in Milan, Summer 1997. (R) JKF Jr. and Carolyn at the Municipal Arts Society gala, February 26, 1996.


(L) Carolyn in Yohji Yamamoto and JFK Jr. at the Municipal Arts Society Gala,  New York City, October 5, 1998. (M) JFK Jr. and Carolyn in New York City. (R) JFK Jr. and Carolyn in Tribeca, New York City, October 1997.

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